Synthesis of CP-88,818 (Tiqueside), An Internal Standard For A Quantitative HPLC/MS Assay System

Article abstract of DOI:10.1016/S0040-4020(01)80399-9

A polydeuterated form of CP-88,818 (1, tiqueside) was needed as an internal standard for a quantitative HPLC/MS assay system. <2,2,3α,4,4-D5>CP-88,818 (11) with undetectable D₀ content was synthesized in five steps from tigogenin (2).The low D₀ content was achieved through two sequential incorporation procedures which gave results superior to those achieved through a single incorporation procedure.A preparatively useful procedure for removing spirostane impurities found in natural occurring tigogenin was also discovered.